(4z,6e)-4,6-undecadienyl trimethylacetate and process for preparing (5z,7e)-5,7-dodecadiene compound therefrom

Abstract

The present invention provides a novel compound, (4Z,6E)-4,6-undecadienyl trimethylacetate (1). The present invention further provides a process for preparing (4Z,6E)-4,6-undecadienyl trimethylacetate (1), the process comprising subjecting a 4-halobutyl trimethylacetate compound (2) wherein X 1 represents a halogen atom, to a phosphonium salt formation reaction with a phosphine compound of the following general formula (3) wherein Ar represents, independently of each other, an aryl group, to obtain a [4-(trimethylacetyloxy)butyl]triarylphosphonium halide compound (4) wherein Y represents a halogen atom, and Ar is as defined above, subjecting the [4-(trimethylacetyloxy)butyl]triarylphosphonium halide compound (4) to a deprotonation reaction in the presence of a base to obtain a reaction product mixture, and subjecting the reaction product mixture to a Wittig reaction with (2E)-2-heptenal (5) to obtain (4Z,6E)-4,6-undecadienyl trimethylacetate (1).

1 . (4Z,6E)-4,6-Undecadienyl trimethylacetate of the following formula (1): 
       
         
           
           
               
               
           
         
       
     
     
         2 . A process for preparing (4Z,6E)-4,6-undecadienyl trimethylacetate of the following general formula (1): 
       
         
           
           
               
               
           
         
         the process comprising:
 subjecting a 4-halobutyl trimethylacetate compound of the following general formula (2): 
 
       
       
         
           
           
               
               
           
         
         wherein X 1  represents a halogen atom, 
         to a phosphonium salt formation reaction with a phosphine compound of the following general formula (3):
   PAr 3   (3)
 
 
         wherein Ar represents, independently of each other, an aryl group, 
         to obtain a [4-(trimethylacetyloxy)butyl]triarylphosphonium halide compound of the following general formula (4): 
       
       
         
           
           
               
               
           
         
         wherein Y represents a halogen atom, and Ar is as defined above,
 subjecting the [4-(trimethylacetyloxy)butyl]triarylphosphonium halide compound (4) to a deprotonation reaction in the presence of a base to obtain a reaction product mixture, and 
 subjecting the reaction product mixture to a Wittig reaction with (2E)-2-heptenal of the following formula (5): 
 
       
       
         
           
           
               
               
           
         
         to obtain (4Z,6E)-4,6-undecadienyl trimethylacetate (1). 
       
     
     
         3 . A process for preparing a (4Z,6E)-1-halo-4,6-undecadiene compound of the following general formula (7): 
       
         
           
           
               
               
           
         
         wherein X 2  represents a halogen atom, 
         the process comprising:
 subjecting (4Z,6E)-4,6-undecadienyl trimethylacetate of the following general formula (1): 
 
       
       
         
           
           
               
               
           
         
         to de-trimethylacetylation to obtain (4Z,6E)-4,6-undecadien-1-ol of the following formula (6): 
       
       
         
           
           
               
               
           
         
         and
 halogenating (4Z,6E)-4,6-undecadien-1-ol (6) to form the (4Z,6E)-1-halo-4,6-undecadiene compound (7). 
 
       
     
     
         4 . A process for preparing (5Z,7E)-5,7-dodecadienal of the following general formula (10): 
       
         
           
           
               
               
           
         
         the process comprising:
 the process according to  claim 3  for preparing the (4Z,6E)-1-halo-4,6-undecadiene compound (7), 
 converting the (4Z,6E)-1-halo-4,6-undecadiene compound (7) into a nucleophilic reagent, (4Z,6E)-4,6-undecadienyl compound, of the following general formula (15): 
 
       
       
         
           
           
               
               
           
         
         wherein M represents Li or MgZ 1 , and Z 1  represents a halogen atom or a (4Z,6E)-4,6-undecadienyl group,
 subjecting the nucleophilic reagent, (4Z,6E)-4,6-undecadienyl compound (15), to a nucleophilic substitution reaction with an orthoformate ester compound (8) of the following general formula (8): 
 
       
       
         
           
           
               
               
           
         
         wherein R represents, independently of each other, an alkyl group having 1 to 6 carbon atoms, 
         to obtain a (5Z,7E)-1,1-dialkoxy-5,7-dodecadiene compound of the following general formula (9): 
       
       
         
           
           
               
               
           
         
         wherein R represents, independently of each other, an alkyl group having 1 to 6 carbon atoms, and
 hydrolyzing the (5Z,7E)-1,1-dialkoxy-5,7-dodecadiene compound (9) to form (5Z,7E)-5,7-dodecadienal (10). 
 
       
     
     
         5 . A process for preparing (5Z,7E)-5,7-dodecadien-1-ol of the following formula 
       
         
           
           
               
               
           
         
         the process comprising:
 the process according to  claim 4  for preparing (5Z,7E)-5,7-dodecadienal (10), and 
 subjecting (5Z,7E)-5,7-dodecadienal (10) to a reduction reaction to form (5Z,7E)-5,7-dodecadien-1-ol (11). 
 
       
     
     
         6 . A process for preparing (5Z,7E)-5,7-dodecadienyl acetate of the following formula (12): 
       
         
           
           
               
               
           
         
         the process comprising:
 the process according to  claim 5  for preparing (5Z,7E)-5,7-dodecadien-1-ol (11), and 
 acetylating (5Z,7E)-5,7-dodecadien-1-ol (11) to form (5Z,7E)-5,7-dodecadienyl acetate (12).